Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2021-09-24 05:34:01 UTC |
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Update Date | 2021-09-24 05:34:01 UTC |
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HMDB ID | HMDB0303909 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one |
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Description | (-)-Nootkatone belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Based on a literature review very few articles have been published on (-)-Nootkatone. |
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Structure | [H][C@@]1(CCC2=CC(=O)C[C@]([H])(C)[C@@]2(C)C1)C(C)=C InChI=1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3/t11-,12-,15+/m0/s1 |
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Synonyms | Value | Source |
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Nootkatone | MeSH | Nootkatone, (4R-(4alpha,4aalpha,6beta))-isomer | MeSH |
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Chemical Formula | C15H22O |
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Average Molecular Weight | 218.34 |
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Monoisotopic Molecular Weight | 218.167065328 |
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IUPAC Name | (4S,4aR,6S)-4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one |
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Traditional Name | (4S,4aR,6S)-4,4a-dimethyl-6-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@]1(CCC2=CC(=O)C[C@]([H])(C)[C@@]2(C)C1)C(C)=C |
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InChI Identifier | InChI=1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3/t11-,12-,15+/m0/s1 |
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InChI Key | WTOYNNBCKUYIKC-SLEUVZQESA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Sesquiterpenoids |
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Direct Parent | Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids |
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Alternative Parents | |
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Substituents | - Eremophilane sesquiterpenoid
- Cyclohexenone
- Cyclic ketone
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | |
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Disposition | Not Available |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one,1TMS,isomer #1 | C=C(C)[C@H]1CCC2=CC(O[Si](C)(C)C)=C[C@H](C)[C@@]2(C)C1 | 1920.6 | Semi standard non polar | 33892256 | 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one,1TMS,isomer #1 | C=C(C)[C@H]1CCC2=CC(O[Si](C)(C)C)=C[C@H](C)[C@@]2(C)C1 | 1805.9 | Standard non polar | 33892256 | 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one,1TMS,isomer #1 | C=C(C)[C@H]1CCC2=CC(O[Si](C)(C)C)=C[C@H](C)[C@@]2(C)C1 | 2074.9 | Standard polar | 33892256 | 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one,1TBDMS,isomer #1 | C=C(C)[C@H]1CCC2=CC(O[Si](C)(C)C(C)(C)C)=C[C@H](C)[C@@]2(C)C1 | 2160.1 | Semi standard non polar | 33892256 | 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one,1TBDMS,isomer #1 | C=C(C)[C@H]1CCC2=CC(O[Si](C)(C)C(C)(C)C)=C[C@H](C)[C@@]2(C)C1 | 2026.5 | Standard non polar | 33892256 | 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one,1TBDMS,isomer #1 | C=C(C)[C@H]1CCC2=CC(O[Si](C)(C)C(C)(C)C)=C[C@H](C)[C@@]2(C)C1 | 2224.0 | Standard polar | 33892256 |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 10V, Positive-QTOF | splash10-014i-0190000000-c24752b1318a3a711643 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 20V, Positive-QTOF | splash10-017i-2930000000-3df119a56dd77df5e286 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 40V, Positive-QTOF | splash10-0gb9-9600000000-83e236a5978c0753f062 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 10V, Negative-QTOF | splash10-014i-0090000000-985cf431add494d4b1ca | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 20V, Negative-QTOF | splash10-014i-0090000000-301348660067d0dbf005 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 40V, Negative-QTOF | splash10-0ukm-1930000000-b1fc47101855e9adbab3 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 10V, Positive-QTOF | splash10-014i-0590000000-341a117f17f53ffe7f34 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 20V, Positive-QTOF | splash10-014i-1930000000-519467321c99880f1dba | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 40V, Positive-QTOF | splash10-001c-5900000000-6f03c86b1c9d475d2571 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 10V, Negative-QTOF | splash10-014i-0090000000-868e2fb00a2cfbf6c529 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 20V, Negative-QTOF | splash10-014i-0090000000-a67ecc985c1a2f05f9c1 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 40V, Negative-QTOF | splash10-015a-0930000000-7dec12d146ded38aa03b | 2021-10-21 | Wishart Lab | View Spectrum |
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